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    Dutchess County, NY Short Term Rental Properties for Sale

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    6 properties
    Duplex with Wood-Burning Fireplace
    Updated: Apr 22
    Duplex with Wood-Burning Fireplace

    32 Old Route 199, Red Hook, NY 12571

    $899,000
    3,500 sqft 4.00 AC lot
    4‑acre property at the end of a long private driveway with expansive decks and porches
    3,500 SF home built in 1976
    Two units separated by one wall, convertible back to single‑family use
    Unit one: four bedrooms, three bathrooms, plus a finished basement
    Unit two: two bedrooms, two bathrooms, successfully used as an Airbnb
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    This listing looks promising.

    Here's a quick look at some key insights for

    32 Old Route 199, Red Hook, NY 12571

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    • Est. Cap Rate

      7.2%
      Above avg (5.9%)

    • Est. NOI

      $65K
      Annual

    • Price @ 7% Cap

      $928K
      Above asking

    • Property Type

      Duplex
      Built 1976
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    Ranch Duplex with Wood-Burning Fireplaces
    Updated: Apr 20
    Ranch Duplex with Wood-Burning Fireplaces

    32 Old Route 199, Red Hook, NY 12571

    $899,000
    4.00 AC lot
    Two ranch living units on a private drive, built in 1976
    4 acres with lawns, pastures, and lightly wooded areas
    Wood‑burning fireplaces plus a wood stove in both units
    Unit One: four bedrooms, three bathrooms, finished lower level
    Unit Two: two bedrooms and two bathrooms with short‑term rental history
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    Waterfront Land with Private Island Retreat
    Waterfront Land with Private Island Retreat

    71 Lake Shore Road, Pine Plains, NY 12567

    $975,000
    0.85 AC lot

    Lakefront mainland barn with electric access plus a private island glamping Airbnb setup with dock, utilities, and views.

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    Two-Unit Residential Income Property
    Two-Unit Residential Income Property

    32 Old Route 199, Red Hook, NY 12571

    $899,000
    4.00 AC lot

    Two spacious living units on four acres, with wood burning fireplaces, wood stove, and pastoral outdoor living spaces.

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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    Turn-Key Estate with Rental History
    Turn-Key Estate with Rental History

    18 Stagecoach Ln, Amenia, NY 12501

    $2,300,000
    4.30 AC lot

    Georgian estate with cottages, renovated for vacation rentals.

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    Seasonal Cottage Near Sylvan Lake
    Seasonal Cottage Near Sylvan Lake

    71 MILLER Rd 5, Hopewell Junction, NY 12533

    $80,000

    Seasonal duplex cottage near Sylvan Lake with amenities.

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    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 6 Active listings in Dutchess County, NY, we suggest exploring several alternatives:

    Dutchess County, NY Short Term Rental Properties Market Trends and Statistics

    Explore 6 short term rental properties for sale in Dutchess County, NY, showcased through 6 active listings on our real estate platform. These investment opportunities span a total of 3,500 square feet of properties for sale, with an estimated market value of $6,052,000.

    Sale prices for short term rental properties in Dutchess County, NY start at $80,000, averaging $1,008,666, and reaching up to $2,300,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Featured Dutchess County Real Estate Agencies

    Realmo connects you with licensed Dutchess County CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Swan Realty of The Hudson Valley
    94 Mill Road #12 Red Hook, NY 12572
    Phone: 18458498315
    swanrealtyhv.com
    MONDELLO UPSTATE PROPERTIES LLC
    37 WEST MARKET ST POB 75 Red Hook, NY
    R. Ferris Real Estate LLC
    1177 Route 55 La Grange, NY 12540
    Phone: 18454547800
    www.ferrisre.com

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